N-methylhydroxylamine hydrochloride → HCID 22123517, compound
Reaction equation
[ClH:1].C[NH:3]O.[CH3:5][O:6][CH:7]([O:17]C)[CH:8]([CH:12](OC)[O:13]C)[C:9]([O-])=[O:10]>O.Cl>[ClH:1].[CH3:5][O:6][C:7]([C:8]1[C:9](=[O:10])[NH:3][O:13][CH:12]=1)=[O:17]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 10 °C
Procedure
To a stirred solution of 2.21 g methylhyroxylamine-hydrochloride in 2.90 g water and 0.26 g concentrated aqueous HCl, 5.81 g 3,3-dimethoxy-2-dimethoxymethyl-propionate were fed over a period of 40 minutes. External cooling with an ice-bath was required in order to keep the temperature between 15° C. and 20° C. After stirring for an additional 15 minutes and cooling to 10° C., a non-stirrable white crystal-pap was gained. The needle-shaped crystals were isolated by suction-filtration, washing with a small amount of diisopropylether and drying in vacuo. Further product-fractions could be isolated by evaporation of part of the mother liquor, filtration, washing, and drying. The total amount of methyl-3-keto-isoxazole-4-carboxylate-hydrochloride obtained in this way was 4.60 g (91% theory based on 3,3-dimethoxy-2-dimethoxymethyl-propionate). Identification of the product was based on 1H-NMR-, 13C- and IR-spectra. The 1H-NMR-spectrum did not show any impurities.
Workup
- temperatureExternal cooling with an ice-bath
- customthe temperature between 15° C. and 20° C
- customThe needle-shaped crystals were isolated by suction-filtration
- washwashing with a small amount of diisopropylether
- customdrying in vacuo
- customFurther product-fractions could be isolated by evaporation of part of the mother liquor, filtration
- washwashing
- customdrying
Sources & evidence
- ORD record
- ord-5b968fceb5fc486088200432ea2ecad6
- Source dataset
- uspto-grants-2000_11
- Patent number
- US06153752
Reaction notes
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